Succinyl-dioxytoluic acid.



. by the addition of ligroin.

UNITED STATES A ENT OFFICE.

RUDOLPH IBERENDES AND JI'J'RGEN GALLSEN, or ELBERFELD, GERMANY, ASSIGNORS T0 .FARBENFABRIKEN VORM. FRIEDR. BAYER & 00., or ELBEBFELD, GERMANY, A 0031 0 RATION OF GERMANY.

SUCCINYL-DIOXYTOLUIC ACID.

Patented Dec. 31, 1907.

Application filed July 22. 1907. 7 Serial No- 38 5.045. Specimens.)

To all whom it may concern:

- 'Be it known, that we, RUDOLPH BERENDES sia, Germany, have invented new and useful Improvements in S110cmyl-D1oxytolu1c Acids,

of which the following is a specification.

Our invention relates to the preparation of the hitherto unknown succinyl-di-oxytoluic acids having the. formula:

which can be prepared by treating oxytoluic acids (cresotinic acids) or its-salts with the acid dihalogenids of succinic acid. According to our researches these products are valuable therapeutic compounds. They vare suitable for use as substitutes for salicylic acid, an average dose being about one gram.

The new products are crystalline compounds bei'ng decomposed into succinic acid and .oxytoluic acid byheating. them with caustic alkalies, being soluble in alcohol and acetone and being scarcely soluble in water.

- In order to illustrate our invention we give the following example, the parts being by weight: 155, parts of succinyl chlorid are slowly added to a solution of 304 parts of para-oxytoluic acid oHnooHcH, i =2 =4 in 500 parts of benzene and 300 parts of dimethylanilin. The addition of the succinyl chlorid is best carried out at a temperature of about 20 C. The mixture is allowed to stand for. some hours. It is then poured into Water and an excess of HCl is added thereto. The .succinyl-di-paraoxytoluic acid separates on stirring for a short time as a solid body, its precipitation is accelerated It is filtered off, washed with water and recrystallized from glacial acetic acid or alcohol. The new compound forms a or stalline powder melting at about 193195 It is odorless and ahnost tasteless,.soluble in hot alcohol and glacial aceticacid and scarcely soluble in water. On boiling the succinyl-di-paraoxytoluic acid with water or'with alkalies it is decomposed,

succinic acid and para-oxytoluic acid being formed.

The following quat1onillustrates the reaction which takes place:

oH,-ooo1- on cH,- oooc,H -oooH H5\ +2HC1 GHQ-COO oooH oH,-oooc,i1,- oooH The succinyl-di-ortho-oxytoluic acid obtainable from ortho-oxytoluic acid (OI-I :QOQH :CH =1 :2 :6) I melts at its-164 o. It' is a crystalline tasteless powder.. .The succinyl-di-metaoxytoluic acid obtainable from meta-oxytoluic acid (OI-I:COOH:GH 1 :2 :5)

Lmelts at 195197 o.

The new succiniyl oxytoluic acids possess the property of orming salts with many metals, for example: the alkaline metals; the hydrogen of the carboxyl groups being replaced by the metal; In this manner either neutral or acid salts may be obtained. The new acidsmay also form salts with organic bases, such as hexamethylentetramin. These salts represent the usual addition products of 1 molecule of the acid and 1 or 2 molecules of the base. All these salts have substantially the same therapeutic effect.

Having now described our invention and in what manner the same is to be performed, what we claim as new and desire to secure .by- Letters Patent is i-- p 1. The herein-described new. succinyl-dioxytoluic acids obtainable by the action of the acid dichlorid of. succinic acid upon oxytoluic acids, which in the acid form are white crystalline powders soluble in alcohol and acetone, scarcely soluble in water and which by heating with caustic alkalies are decomposed into succinic acid and oxyto luic acids, forming salts with bases which retain the valuable therapeutic properties exhibited by the acids, substantially as hereinbefore described.

2. The herein-described new succinyl-diparaoxytoluic acid obtainable by the action of the acid dichlorid of succinic acid upon para-oxytoluicacid, which in the acid formis a white crystalline powder melting at 193195 0., soluble in hot alcohol and oxyteluic acid, formin salts with basesl l glacial acetic acid, scarcely soluble in water set our hands 1n the presence of lrm suband \VhlCll by heating with caustic alkalies is scribing witnesses. decomposed into succmlc acid and para- RUDOLPH BEREXDES [IN SJ JURGEX CALLSEX. [1 s] Witnesses:

OTTO 116x10, OSKAR Kmm.

which retain the valuable therapeutic properties exhibited by the acid, substantially as hereinbefore described.

In testimony whereof we have hereunto 

